Triethylsilane → [Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester

HRID 479145Notes

Reaction equation

HRID 479145 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH:5]([O:36][CH3:37])[CH:6](O)[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])=[CH:9][CH:8]=1)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:38])[CH:5]([O:36][CH3:37])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[O:24][C:25]=2[CH3:26])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 695567193-Hydroxy-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester

Product 1

HCID 69556683[Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl esterYield 64.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.228 g of the above prepared 3-hydroxy-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester (0.44 mmol) was dissolved in 2.3 ml of trifluoroacetic acid, treated at 0° with 0.697 ml of triethylsilane (10 eq.) and then kept for 4 h at 0°. The reaction mixture was then poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed twice with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 0.143 g of the title compound as colorless oil.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe organic layer washed twice with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-78f7e8b44396410eb73ff0ada8bebe63
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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